Caribbean

Escape the Cold to Enjoy Caribbean Getaways

Have you considered the Caribbean as your winter escape destination? With its picturesque landscapes, year-round warmth, and abundance of activities, it's no wonder the Caribbean remains one of the top warm winter destination spots. Whether you're looking for a tranquil escape to a secluded sandy beach, a bustling cultural experience, or an action-packed adventure, there are Caribbean getaways for all types of travelers — and all within close proximity on this target-shaped archipelago.

A great combination of islands to explore while soaking up the sun is the Greater Antilles, the largest island chain in the Caribbean Sea. This archipelagic group of islands consists of four large islands — Cuba, Jamaica, Hispaniola, and Puerto Rico — as well as several dozen smaller islands.

Take In a Different Culture in Cuba

For travelers looking to combine culture and adventure, look no further than Cuba. Rich in colonial history and vibrant culture, Cuba offers unique beachfront cities, sugar mill plantations, and a mix of old and modern bustling capitals. Starting in the capital of Havana, visit renowned landmarks such as Plaza de la Revolución and take a classic car ride around the city. Consider embarking on a road trip to scenic Viñales Valley for incredible views of lush green hills and tobacco plantations.

Soak Up the Sun in Jamaica

The Caribbean island of Jamaica, located just south of Cuba, offers travelers the perfect combination of breathtaking landscapes, pulsing reggae music, and laidback vibes. Tourists flock to Jamaica to visit its famed resorts, experience its lively nightlife, and explore its stunning mountains and hidden waterfalls. Spend your days soaking up the sun on the stunning Seven-Mile Beach in Negril or go for a dip in the world-famous Dunn's River Falls. Pay a visit to the historic capital of Kingston, the art-rich Ocho Rios, or lively Montego Bay.

Exploration on Hispaniola Island

Located on the island of Hispaniola near the Dominican Republic, Haiti provides adventure seekers with breathtaking landscapes and colorful culture. From its cascading waterfalls to its bustling markets, there is something for everyone in Haiti. Explore the captivating Citadelle Laferrière, explore the busy streets of Cap-Haïtien, and take a dip in the blue waters of Labadee. Or head to Kenscoff National Park to admire the lush rainforest and spot some of the island's native wildlife.

Experience the Island Life in Puerto Rico

Known as the “Island of Enchantment,” Puerto Rico is a U.S. territory that promises travelers unique experiences and spectacular natural landscapes. Enjoy the tranquil Caribbean vibes as you explore the small towns, sandy beaches, and traditional fishing villages. Take a trip to the El Yunque rainforest or San Juan's old town, then immerse yourself in Puerto Rico's vibrant culture and unique cuisine. Enjoy a night out in San Juan or dance the night away to the pulsing Latin beats in Rincon's Tamboo Bar.